Research Progress of Photoelectric Co-catalysis

doi:10.6023/cjoc202106051

Abstract

Photochemical and electrochemical reactions, which are mild and green, have been widely used in organic synthesis in recent years. To push the limits of both synthetic technologies, organic chemists have focused on using these two strategies to promote organic transformation in a single reaction system. A series of photoelectrochemical strategies have been developed, and the main one at present is electrochemically mediated photoredox catalysis. In addition, photoexcitation-assisted electroredox strategies have also gradually shown their potential in organic synthesis. These strategies realize the complementary advantages and disadvantages of photochemistry and electrochemistry, and can solve the problems that can not be solved by a single synthetic technology, such as removing oxidizing reducing agents that complicate the reaction, generating intermediates with high activity under mild conditions, and so on. In this paper, the research progress of photoelectrochemical strategies is summarized according to the existing photoelectric catalysis reactions, and the possible mechanism of some reactions is discussed.

Key words: photoredox catalysis, electrocatalysis, photoelectrochemistry

Cite this article

Yingjie Liu, Zhichuan Wang, Jianping Meng, Chen Li, Kai Sun. Research Progress of Photoelectric Co-catalysis[J]. Chinese Journal of Organic Chemistry, 2022, 42(1): 100-110.

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Fig. & Tab. 28

Figure 1. Schematic diagram of electrochemical reaction

Figure 2. Photocatalytic cycle

Figure 3. Photoelectrocatalysis

Scheme 1. Trifluoromethylation of aromatic hydrocarbon C―H under photoelectric catalysis

Scheme 2. Alkylation of C―H heteroaromatics with organic trifluoroborate under photoelectric catalysis

Scheme 3. Alkylation mechanism of nitrogen ortho-position under photoelectric catalysis of 4-methylquinoline

Scheme 4. Photoelectric decarboxylation of heterocyclic aromatic hydrocarbons with carboxylic and oxalic acids by C―H alkylation and carbamylation

Scheme 5. C―H alkylation of heterocyclic aromatic hydrocarbons with alkyl oxalate

Scheme 6. Photoelectrocatalytic azide reaction of C(sp3)―H bond

Scheme 7. Azidation mechanism of C(sp3)―H bond under photoelectric catalysis

Scheme 8. Photoelectric reaction of alcohol co-catalyzed by RFT and TU

Scheme 9. Photoelectric reaction mechanism of alcohol co- catalyzed by RFT and TU

Scheme 10. Dehydrogenation cross-coupling of benzothiazole with aliphatic hydrogen donors

Scheme 11. Electrophotocatalytic C―H azolation of aromatic hydrocarbons

Scheme 12. Electrophotocatalytic coupling of arenes and nitrogen heteroaromatics

Scheme 13. C―H/N―H coupling reaction mechanism of benzene and 1H-pyrazole-4-ethyl carboxylate under photoelectric catalysis

Scheme 14. Electrophotocatalytic SNAr of unactivated aryl fluorides

Scheme 15. C-C and C-N coupling reactions of ether ortho sites under photoelectric catalysis

Scheme 16. Electrophotocatalytic synthesis of 3,4-dihydro- imidazole

Scheme 17. Electrophotocatalytic synthesis of 2-oxazoline

Scheme 18. Photoelectrocatalytic borylation of aryl halides

Scheme 19. Reaction mechanism of aryl radical generation by photoelectric catalysis of aryl halides

Scheme 20. Photoelectrocatalytic phosphorylation of aryl chloride

Scheme 21. Photoelectrocatalytic aziridination of olefin

Scheme 22. Mechanism of photoelectrocatalytic aziridination of olefin

Scheme 23. C―H amination mediated by iodide

Scheme 24. Reaction mechanism of iodide-mediated C―H amination

Scheme 25. Dehydrogenation cross-coupling of heteroaromatics with C(sp3)―H donors

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